Synthesis of phenyliodine(III) bis(3-bromopropionate) for an organocatalyzed Markovnikov-type bromo-aminoxidation of vinylarenes

Abstract

An organocatalytic Markovnikov-type bromo-aminoxidation of styrene derivatives was achieved by using in-situ-generated bromine and N-oxyl radicals, and the desired products were obtained in moderate to good yields. The bromine radical was generated from phenyliodine(III) bis(3-bromopropionate) through consecutive decarboxylation and deethylenation reactions via an organocatalytic SET process. Phenyliodine(III) bis(3-bromopropionate) also served as the oxidant for the generation of the N-oxyl radicals, while the N-oxyl radical was also crucial for the generation of the key β-enaminyl radical intermediate that was required for the SET process.

Keywords

• Organocatalysis
• Phenyliodine(III) dicarboxylate
• Bromo-aminoxidation
• Styrene
• Radical decarboxylation
• SET reaction